EP3708159B1 - Ginkgo-diterpen-lacton-zusammensetzung - Google Patents

Ginkgo-diterpen-lacton-zusammensetzung Download PDF

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Publication number
EP3708159B1
EP3708159B1 EP18894739.4A EP18894739A EP3708159B1 EP 3708159 B1 EP3708159 B1 EP 3708159B1 EP 18894739 A EP18894739 A EP 18894739A EP 3708159 B1 EP3708159 B1 EP 3708159B1
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EP
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Prior art keywords
group
composition
diterpene lactone
ginkgo
ginkgo diterpene
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Active
Application number
EP18894739.4A
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English (en)
French (fr)
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EP3708159A1 (de
EP3708159A4 (de
Inventor
Wei Xiao
Enli ZHOU
Zeyu Cao
Xiujuan CHANG
Xiaodong KANG
Yongxiang Wang
Hanfei HU
Yun Wu
Zhenzhong Wang
Chenfeng Zhang
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Jiangsu Kanion Pharmaceutical Co Ltd
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Jiangsu Kanion Pharmaceutical Co Ltd
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Publication of EP3708159A4 publication Critical patent/EP3708159A4/de
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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/16—Ginkgophyta, e.g. Ginkgoaceae (Ginkgo family)
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/365—Lactones
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/24—Antidepressants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P39/00—General protective or antinoxious agents
    • A61P39/06—Free radical scavengers or antioxidants

Definitions

  • the present invention belongs to the technical field of medicine and in particular to a ginkgo diterpene lactone composition.
  • Ginkgo tree is also known as maidenhair tree. It is also called Yajiao tree or Gongsun tree in ancient times. It is one of the oldest tree species in the world and its resources are most widely distributed in China, accounting for more than 70% of the world total. Ginkgo has been used medicinally for 600 years. Ginkgo biloba leaves have a wide range of biological activities and contain a variety of chemical components, including flavonoids, terpenes, polyphenols, phenylpropanoids, organic acids, sugars, fatty acids, lipids, inorganic salts and amino acids. Modern pharmacological studies have proven that Ginkgo biloba extract has anti-oxidant and anti-aging effects and is also capable of lowering blood pressure, promoting blood circulation, and improving brain function.
  • Ginkgolides are terpenoids and are known as terpene lactones. In 1967, Professor Nakanishi Koji of Columbia University in the United States first reported four diterpene lactones with special structures, namely Ginkgolides A, B, C and M (GA, GB, GC, and GM). Ginkgolide J (GJ) was isolated in 1987, and Ginkgolides K and L (GK and GL) were later discovered. Ginkgolides are unique and important components of Ginkgo biloba, with specific anti-PAF (Platelet Activating Factor) activity. They are natural strong PAF antagonists (PAF is an endogenous phospholipid produced by platelets and a variety of inflammatory tissues.
  • PAF Plate Activating Factor
  • PAF antagonists have antioxidant, anti-inflammatory, anti-platelet aggregation, antiapoptosis, anti-cell death and angiectatic pharmacological effects and also can protect nervous centralis and ischemic tissue. They have unique advantages especially in the treatment of ischemic stroke.
  • CN1424031A reports a ginkgolide preparation, containing 30-40% of GA, 50-65% of GB, and 0.5 -5% of GK. Based on the theory of traditional Chinese medicine, traditional Chinese medicine emphasizes the synergistic effect of multiple ingredients. Based on this, the inventors found that when the composition contains GC, GJ, and GL, it will increase the pharmacological effects of the ginkgolide composition in some way.
  • the present invention is intended to find a composition with higher pharmacological activity on the basis of the synergy effect between the ginkgolide monomers.
  • the present invention provides a ginkgo diterpene lactone composition, comprising, by weight: 32-36 parts of GA, 55-58 parts of GB, 2.2-3.4 parts of GK, wherein, the composition further comprises GC, GJ, and GL, and the total content of GC, GJ and GL is above 2.6 parts.
  • the content of each of GC, GJ and GL is not less than 0.5 part.
  • the total content of GC, GJ and GL is 10.8 parts or less.
  • the total content of GC, GJ and GL is between 2.6-10.8 parts.
  • the total content of GC, GJ and GL is between 3.0 - 6.0 parts.
  • the total content of GC, GJ and GL is between 4.6 parts.
  • the present invention provides a ginkgo diterpene lactone composition, comprising, by weight: 32-34% of GA, 56-58% of GB, and 2.4-3.4% of GK, wherein the composition further comprises GC, GJ and GL, and the total content of GC, GJ and GL is above 2.6%.
  • the content of each of GC, GJ and GL is not less than 0.5%.
  • the total content of GC, GJ and GL is between 2.6% and 10.8%.
  • the total content of GC, GJ and GL is between 3.0% and 6.0%.
  • the total content of GC, GJ and GL is 4.6%.
  • the composition does not comprise bilobalides.
  • the present invention further provides a ginkgo diterpene lactone preparation containing the above composition, wherein the preparation further comprises pharmaceutically acceptable excipients.
  • the present invention further provides a ginkgo diterpene lactone injection containing the above composition.
  • the injection is in a dose of 1 ml or 5 ml or 10 ml and contains 5 ⁇ 0.5 mg or 25 ⁇ 0.5 mg or 50 ⁇ 0.5 mg of the ginkgo diterpene lactone composition respectively. Further, the injection further contains meglumine and sodium chloride, and the weight ratio of the ginkgo diterpene lactone composition to meglumine to sodium chloride is (2-8): (2-8): (4-12).
  • the present invention further provides an application of the above composition in the preparation of an antidepressant drug.
  • the present invention further provides an application of the above composition in the preparation of a drug for preventing and/or treating cardiovascular and cerebrovascular diseases.
  • the present invention further provides an application of the above composition in the preparation of a drug for ameliorating oxidative stress.
  • the wording "application” refers to administering the above-mentioned extract to a subject having a corresponding disease or a pre-disposition to the disease, with the purpose of conferring a therapeutic effect, such as curing, alleviating, changing, influencing, improving or preventing the disease, its symptoms, or its predisposition.
  • a therapeutic effect such as curing, alleviating, changing, influencing, improving or preventing the disease, its symptoms, or its predisposition.
  • the present invention utilizes a mouse model to confirm that the ginkgo diterpene lactone composition can extend the tail flick interval and the swimming interval to varying degrees, and also can increase the number of escapes from electric shock to varying degrees; moreover, due to further addition of a certain amount of GC, GJ and GL, the effect of the composition in improving the depression state is greatly improved.
  • the present invention also confirms that after the administration of the ginkgo diterpene lactone composition, SOD, MDA, GSH, and TAC and other indicators can be improved to varying degrees; especially after the addition of a certain amount of GC, GJ, and GL, these improvements are more obvious; the level of oxidative stress can be better improved and the oxidative damage can be relieved.
  • the wording "above” in the present invention includes the number, for example, above 2.6, including 2.6; and for another example, above 2.6%, including 2.6%.
  • Test drugs Each Ginkgo diterpene lactone compound is a commercially available standard product, and the gingko diterpene lactone composition groups A-K with different ratios of components were formulated according to the ratios described in the table below, and then dissolved with 0.5% meglumine and 0.15% citric acid to prepare experimental solutions.
  • the positive drug was imipramine hydrochloride tablets (provided by Shanghai Jiufu Pharmaceutical Co., Ltd., 25 mg/tablet), which were formulated into 12.5 mg/mL and 5 mg/mL solutions.
  • mice Healthy male mice weighing 20-24 g were selected and randomly divided into model group, positive drug group and ginkgo diterpene lactone composition groups A-K, with 10 rats in each group.
  • the mice in the positive drug group were orally administered with imipramine tablets in a daily dose of 50 mg/kg, and the mice in the Ginkgo diterpene lactone composition groups A-K were administered in a daily dose of 9 mg/kg (ig), once a day for 5 consecutive days.
  • the experiment was started 30 minutes after the fifth administration.
  • a 2 cm portion of the tail of the mouse was affixed to a wooden stick to make the animal upside down, and its head was about 5 cm from the ground.
  • the lines of sight of the animals were blocked with plates on both sides, and the immobility time of the animals in the last 3 minutes of 6 minutes. It was measured once before the administration and once 5 days after the administration. The difference between the two immobility times of the mice themselves were calculated and then statistical analysis was conducted after Ig (X + 86) conversion.
  • mice Male mice weighing 20-24 g were selected, grouped and administered in the same manner as in Section 2.1. The experiment was started 30 minutes after the fifth administration. The mice were placed in a graduated cylinder (20 cm in height and 14 cm in diameter) with 30 °C water in the depth of 10 cm. The difference between the two immobility times of the mice themselves were calculated and then statistical analysis was conducted after Ig (X + +45) conversion.
  • a 20 ⁇ 10 ⁇ 10 cm cage having copper bars at the bottom was used to give the animals 60 random inescapable electric shock in the foot (0.85 mA, 15s, once every 1 min), rats in the normal group were placed in the same cage but not subjected to the electric shock. 48 hours later, avoidance training was started.
  • a 20 ⁇ 10 ⁇ 10 cm shuttle box with a copper bar spacing of 1 cm at the bottom was used. The animals were individually placed at one end in the shuttle box and allowed to get adapted for 5min, and then subjected to avoidance training for 20 times at an interval of 30s. During the training, a light signal is sent first to allow the animals to reach the other end during this period to avoid electric shock.
  • the light signal will continue for another 3s, accompanying by a 0.8 mA, 3s foot shock. If the rats still had no response, the electric shock and light signal were stopped immediately and an escape failure record was made. The training was conducted for 5 days, and the number of successful escapes of each rat during training was recorded every day, and the results of the fifth training were counted.
  • Test drugs Each Ginkgo diterpene lactone compound is a commercially available standard product, and the gingko diterpene lactone composition groups A-K with different ratios of components were formulated according to the ratios described in the above table, and then dissolved with 0.5% meglumine and 0.15% citric acid to prepare experimental solutions.
  • the positive drug was edaravone injection (Nanjing Simcere Dongyuan Pharmaceutical Co., Ltd., 30mg/injection).
  • Modeling and administration Healthy male rats were selected and randomly divided into normal group, model group, positive drug group and ginkgo diterpene lactone composition groups A-K, With the exception of the normal group, the other groups were orally administrated with alcohol with a daily dose of 6 g/kg. Rats in the positive drug group were administrated with edaravone injection (iv) in a daily dose of 6.25 mg/kg, and rats in the ginkgo diterpene lactone composition groups A-K were administrated in a daily dose of 3 mg/kg (iv), they were continuously administrated or given alcohol for 5 weeks.
  • edaravone injection iv
  • rats in the ginkgo diterpene lactone composition groups A-K were administrated in a daily dose of 3 mg/kg (iv), they were continuously administrated or given alcohol for 5 weeks.
  • oxidative stress After the administration, rats in each group were anesthetized with 10% chloral hydrate, abdominal aortic blood was collected and then subjected to heparin anticoagulation to separate serum; changes of MDA, SOD, GSH and TAC levels in the serum were detected according to the instructions of the kits, and the protein content of each sample was measured using the BCA protein test kit.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Dermatology (AREA)
  • Biochemistry (AREA)
  • Pain & Pain Management (AREA)
  • Psychiatry (AREA)
  • Toxicology (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Natural Medicines & Medicinal Plants (AREA)
  • Microbiology (AREA)
  • Mycology (AREA)
  • Vascular Medicine (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Alternative & Traditional Medicine (AREA)
  • Biotechnology (AREA)
  • Urology & Nephrology (AREA)
  • Medical Informatics (AREA)
  • Botany (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Molecular Biology (AREA)
  • Medicines Containing Plant Substances (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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Claims (9)

  1. Ginkgo-Diterpenlactonzusammensetzung, umfassend, nach Gewicht: zu 32-36 Gew.-% GA, zu 55-58 Gew.-% GB und zu 2,2-3,4 Gew.-% GK, wobei die Zusammensetzung ferner GC, GJ und GL in einem Gesamtgehalt von über 2,6 Gew.-% und jeweils nicht weniger als 0,5 Gew.-% umfasst.
  2. Zusammensetzung nach Anspruch 1, wobei der Gesamtgehalt an GC, GJ und GL 2,6-10,8 Gew.-%, vorzugsweise 3,0-6,0 Gew.-% und am meisten bevorzugt 4,6 Gew.-% der Zusammensetzung ausmacht.
  3. Ginkgo-Diterpenlactonzubereitung, die die Zusammensetzung nach Anspruch 1 oder 2 enthält, wobei die Zubereitung ferner pharmazeutisch akzeptable Hilfsstoffe umfasst.
  4. Ginkgo-Diterpenlactoninjektion, die die Zusammensetzung nach Anspruch 1 oder 2 enthält.
  5. Injektion nach Anspruch 4, wobei die Injektion in einer Dosis von 1 ml oder 5 ml oder 10 ml vorliegt und jeweils 5 ± 0,5 mg oder 25 ± 0,5 mg oder 50 ± 0,5 mg der Ginkgo-Diterpenlactonzusammensetzung enthält.
  6. Injektion nach Anspruch 4 oder 5, ferner enthaltend Meglumin und Natriumchlorid, wobei das Gewichtsverhältnis der Ginkgo-Diterpenlactonzusammensetzung zu Meglumin und Natriumchlorid (2-8):(2-8):(4-12) beträgt.
  7. Zusammensetzung nach Anspruch 1 oder 2 zur Verwendung bei der Behandlung von Depression.
  8. Zusammensetzung nach Anspruch 1 oder 2 zur Verwendung bei der Behandlung von kardiovaskulären und zerebrovaskulären Krankheiten.
  9. Zusammensetzung nach Anspruch 1 oder 2 zur Verwendung bei der Behandlung von Stress.
EP18894739.4A 2017-12-29 2018-11-13 Ginkgo-diterpen-lacton-zusammensetzung Active EP3708159B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CN201711475539.2A CN107929283B (zh) 2017-12-29 2017-12-29 银杏二萜内酯组合物
PCT/CN2018/115167 WO2019128499A1 (zh) 2017-12-29 2018-11-13 银杏二萜内酯组合物

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EP3708159A1 EP3708159A1 (de) 2020-09-16
EP3708159A4 EP3708159A4 (de) 2020-11-25
EP3708159B1 true EP3708159B1 (de) 2023-09-13

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US (1) US11524041B2 (de)
EP (1) EP3708159B1 (de)
JP (1) JP6976446B2 (de)
KR (1) KR102537631B1 (de)
CN (1) CN107929283B (de)
WO (1) WO2019128499A1 (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107929283B (zh) * 2017-12-29 2019-05-07 江苏康缘药业股份有限公司 银杏二萜内酯组合物
CN107898782B (zh) * 2017-12-29 2019-03-26 江苏康缘药业股份有限公司 一种银杏二萜内酯组合物

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1279903C (zh) * 2002-08-23 2006-10-18 江苏康缘药业股份有限公司 含有银杏内酯的制剂及其制备工艺
CN100402024C (zh) * 2004-01-14 2008-07-16 海口龙南医药科技开发有限公司 一种银杏内酯冻干粉针剂及其制备方法
CN100569234C (zh) 2005-03-30 2009-12-16 沈阳药科大学 具有神经保护作用的银杏总内酯组合物
CN100479816C (zh) 2005-12-05 2009-04-22 浙江海正药业股份有限公司 银杏内酯配伍药物组合物及其制备方法和用途
CN104914174B (zh) 2014-03-16 2017-07-25 江苏康缘药业股份有限公司 一种注射用银杏二萜内酯的含量测定方法
CN105853479A (zh) 2016-01-12 2016-08-17 江西中医药大学 一种用于抑郁症的药物组合物
CN106377517A (zh) * 2016-11-25 2017-02-08 遵义医学院 银杏内酯‑pvp纳米粒及其制备方法
CN107929283B (zh) 2017-12-29 2019-05-07 江苏康缘药业股份有限公司 银杏二萜内酯组合物

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Publication number Publication date
KR20200097304A (ko) 2020-08-18
EP3708159A1 (de) 2020-09-16
CN107929283B (zh) 2019-05-07
KR102537631B1 (ko) 2023-05-26
US20210196773A1 (en) 2021-07-01
JP6976446B2 (ja) 2021-12-08
JP2021508723A (ja) 2021-03-11
CN107929283A (zh) 2018-04-20
WO2019128499A1 (zh) 2019-07-04
EP3708159A4 (de) 2020-11-25
US11524041B2 (en) 2022-12-13

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